JPH01272557A - 2,6-diethyl-4-phenozxyaniline derivative and production thereof - Google Patents
2,6-diethyl-4-phenozxyaniline derivative and production thereofInfo
- Publication number
- JPH01272557A JPH01272557A JP9907088A JP9907088A JPH01272557A JP H01272557 A JPH01272557 A JP H01272557A JP 9907088 A JP9907088 A JP 9907088A JP 9907088 A JP9907088 A JP 9907088A JP H01272557 A JPH01272557 A JP H01272557A
- Authority
- JP
- Japan
- Prior art keywords
- compound
- formula
- compound expressed
- general formula
- reaction
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 8
- 150000001875 compounds Chemical class 0.000 claims abstract description 17
- 125000005843 halogen group Chemical group 0.000 claims abstract description 8
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 6
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 5
- 229910052751 metal Inorganic materials 0.000 claims abstract description 4
- 239000002184 metal Substances 0.000 claims abstract description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims 4
- YIGSSIGFLCAXDP-UHFFFAOYSA-N CCC1=CC(=CC(=C1N)CC)OC2=CC=CC=C2 Chemical class CCC1=CC(=CC(=C1N)CC)OC2=CC=CC=C2 YIGSSIGFLCAXDP-UHFFFAOYSA-N 0.000 claims 1
- -1 Diethyl-4-phenoxyaniline derivative Chemical class 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract description 6
- 238000006243 chemical reaction Methods 0.000 abstract description 5
- 239000002904 solvent Substances 0.000 abstract description 5
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 abstract description 4
- 230000002363 herbicidal effect Effects 0.000 abstract description 4
- 239000005749 Copper compound Substances 0.000 abstract description 3
- 239000003054 catalyst Substances 0.000 abstract description 3
- 150000001880 copper compounds Chemical class 0.000 abstract description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 abstract description 2
- 239000003905 agrochemical Substances 0.000 abstract description 2
- 229910052783 alkali metal Inorganic materials 0.000 abstract description 2
- 150000001340 alkali metals Chemical class 0.000 abstract description 2
- BERDEBHAJNAUOM-UHFFFAOYSA-N copper(I) oxide Inorganic materials [Cu]O[Cu] BERDEBHAJNAUOM-UHFFFAOYSA-N 0.000 abstract description 2
- 229960004643 cupric oxide Drugs 0.000 abstract description 2
- KRFJLUBVMFXRPN-UHFFFAOYSA-N cuprous oxide Chemical compound [O-2].[Cu+].[Cu+] KRFJLUBVMFXRPN-UHFFFAOYSA-N 0.000 abstract description 2
- 229940112669 cuprous oxide Drugs 0.000 abstract description 2
- 239000003814 drug Substances 0.000 abstract description 2
- 229910052700 potassium Inorganic materials 0.000 abstract description 2
- 239000011591 potassium Substances 0.000 abstract description 2
- 229910052708 sodium Inorganic materials 0.000 abstract description 2
- 239000011734 sodium Substances 0.000 abstract description 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 229940079593 drug Drugs 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 2
- ZPSJGADGUYYRKE-UHFFFAOYSA-N 2H-pyran-2-one Chemical compound O=C1C=CC=CO1 ZPSJGADGUYYRKE-UHFFFAOYSA-N 0.000 description 2
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 229940053202 antiepileptics carboxamide derivative Drugs 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 2
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 2
- QTMDXZNDVAMKGV-UHFFFAOYSA-L copper(ii) bromide Chemical compound [Cu+2].[Br-].[Br-] QTMDXZNDVAMKGV-UHFFFAOYSA-L 0.000 description 2
- 229940045803 cuprous chloride Drugs 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- 239000011968 lewis acid catalyst Substances 0.000 description 2
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- IQHSSYROJYPFDV-UHFFFAOYSA-N 2-bromo-1,3-dichloro-5-(trifluoromethyl)benzene Chemical group FC(F)(F)C1=CC(Cl)=C(Br)C(Cl)=C1 IQHSSYROJYPFDV-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 229910021589 Copper(I) bromide Inorganic materials 0.000 description 1
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 1
- 229910021590 Copper(II) bromide Inorganic materials 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- HOPRXXXSABQWAV-UHFFFAOYSA-N anhydrous collidine Natural products CC1=CC=NC(C)=C1C HOPRXXXSABQWAV-UHFFFAOYSA-N 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- UTBIMNXEDGNJFE-UHFFFAOYSA-N collidine Natural products CC1=CC=C(C)C(C)=N1 UTBIMNXEDGNJFE-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- NKNDPYCGAZPOFS-UHFFFAOYSA-M copper(i) bromide Chemical compound Br[Cu] NKNDPYCGAZPOFS-UHFFFAOYSA-M 0.000 description 1
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 1
- GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 description 1
- 229960003280 cupric chloride Drugs 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- HPYNZHMRTTWQTB-UHFFFAOYSA-N dimethylpyridine Natural products CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- GYNAVKULVOETAD-UHFFFAOYSA-N n-phenoxyaniline Chemical class C=1C=CC=CC=1NOC1=CC=CC=C1 GYNAVKULVOETAD-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
【発明の詳細な説明】
（産業上の利用分野）
本発明は、医薬、農薬等の製造中間体として有用な新規
な２，６−ジニチルアニリン誘導体及びその製造法に関
する。本発明化合物は、特に除草活性を有するピロン、
３．カルボキサミド誘導体（特願昭６２−５３８７３）
の製造中間体として有用である。DETAILED DESCRIPTION OF THE INVENTION (Field of Industrial Application) The present invention relates to a novel 2,6-dinitylaniline derivative useful as an intermediate in the production of pharmaceuticals, agricultural chemicals, etc., and a method for producing the same. The compounds of the present invention particularly include pyrone, which has herbicidal activity;
3. Carboxamide derivatives (patent application No. 62-53873)
It is useful as an intermediate in the production of
（従来技術および発明が解決しようとする課題）本発明
化合物は、本発明者らによって初めて合成された新規化
合物である。本発明者らは、除草活性を有するピロン−
３，カルボキサミド誘導体の製造法について検討した結
果、本発明化合物がその製造中間体として重要であるこ
とおよびこの有利な製造法を見い出し本発明に至った。(Prior Art and Problems to be Solved by the Invention) The compound of the present invention is a novel compound synthesized for the first time by the present inventors. The present inventors have discovered that pyrone, which has herbicidal activity,
3. As a result of studying methods for producing carboxamide derivatives, we discovered that the compound of the present invention is important as an intermediate for its production and found an advantageous production method thereof, leading to the present invention.
（課題を解決するための手段）
本発明は一般式（１）：
（Ｒは水素原子、低級アルキル基、低級アルコキシ基又
はハロゲン原子を示す。）で表される２、６−ジエチル
−４−フェノキシアニリン誘導体及びその製造法に関す
る。(Means for Solving the Problems) The present invention provides 2,6-diethyl-4- represented by the general formula (1): (R represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, or a halogen atom). This invention relates to phenoxyaniline derivatives and methods for producing the same.
一般式（Ｉ）の化合物のＲにおける低級アルキル基とし
ては、メチル、エチル、イソプロピル、ブチル基などが
、低級アルコキシ基としては、メトキシ、エトキシ基な
どが又、ハロゲン原子としては、フッ素原子、塩素原子
などが含まれる。水素原子以外の直換基を複数個有する
場合も含まれる。Examples of the lower alkyl group in R of the compound of general formula (I) include methyl, ethyl, isopropyl, and butyl groups; examples of the lower alkoxy group include methoxy and ethoxy groups; and examples of the halogen atom include fluorine atom and chlorine. Includes atoms, etc. It also includes cases where it has a plurality of direct substituents other than hydrogen atoms.
本発明における一般式（Ｉ）の化合物は、一般式（ＩＩ
） ：
ｔ
ｔ
（Ｘはハロゲン原子を示す。）で表される化合物と一般
式（ＩＩＩ）：
（Ｍは金属、Ｒは前記と同じ意味を示す。）で表される
化合物とを反応させることによって製造することが出来
る。The compound of general formula (I) in the present invention is a compound of general formula (II)
) : t t (X represents a halogen atom) A compound represented by the general formula (III): (M is a metal, R represents the same meaning as above) is reacted. It can be manufactured by
Ｘは、ハロゲン原子を表すが、反応性の良さから特に、
臭素あるいはヨウ素が好ましい。Ｍで示される金属とし
ては、ナトリウム、カリウムなどのアルカリ金属が挙げ
られる。X represents a halogen atom, and because of its good reactivity,
Bromine or iodine is preferred. Examples of the metal represented by M include alkali metals such as sodium and potassium.
本発明の方法においては、触媒として銅化合物を用いる
ことが好ましい。銅化合物としては、酸化第一銅、酸化
第二銅、ヨウ化第−銅、ヨウ化第二銅、塩化第一銅、塩
化第二銅、臭化第一銅および臭化第二銅などが挙げられ
る。これらは、混合して用いてもよい。In the method of the present invention, it is preferable to use a copper compound as a catalyst. Examples of copper compounds include cuprous oxide, cupric oxide, cuprous iodide, cupric iodide, cuprous chloride, cupric chloride, cuprous bromide, and cupric bromide. Can be mentioned. These may be used in combination.
この反応は、無溶媒で行うことができるが、溶媒を用い
てもよい。溶媒の具体例としては、ベンゼン、ヘキサン
、シクロヘキサン、デカリン、トルエン、キシレン、メ
シチレン、Ｎ、Ｎ−ジメチルホルムアミド、ジメチルス
ルホキシド、ジブチルエーテル、ジメトキシエタン、ジ
エチレングリコールジメチルエーテル、コリジン、ルチ
ジン、ピリジンなどが挙げられる。This reaction can be carried out without a solvent, but a solvent may also be used. Specific examples of the solvent include benzene, hexane, cyclohexane, decalin, toluene, xylene, mesitylene, N,N-dimethylformamide, dimethyl sulfoxide, dibutyl ether, dimethoxyethane, diethylene glycol dimethyl ether, collidine, lutidine, pyridine, and the like.
本発明の反応における温度は特に限定されず広い温度範
囲で選びうるが、一般には５０〜２２０°Ｃ１好ましく
は１００〜２００°Ｃの範囲から選ぶと良い。The temperature in the reaction of the present invention is not particularly limited and can be selected within a wide temperature range, but it is generally selected from the range of 50 to 220°C, preferably 100 to 200°C.
本発明の化合物の精製方法は、特に、限定されるもので
はない。一般には、触媒のろ別、中和処理、抽出、蒸留
、カラムクロマトグラフィー等によって精製することが
できる。又、本発明の化合同じ意味を表す）で表される
化合物なルイス酸触媒存在下エチレンを加圧下に作用さ
せることによって製造することもできる。この場合、ル
イス酸触媒として塩化アルミニウムが好適に用いられる
。The method for purifying the compound of the present invention is not particularly limited. In general, it can be purified by filtering off the catalyst, neutralization, extraction, distillation, column chromatography, etc. It can also be produced by treating ethylene under pressure in the presence of a Lewis acid catalyst. In this case, aluminum chloride is preferably used as the Lewis acid catalyst.
尚、本発明の製造法によって得られる本発明の化合物（
Ｉ）から例えば、下記ルートによって、−般式（ＩＶ）
で示される除草活性を有する化合物が得られる。In addition, the compound of the present invention obtained by the production method of the present invention (
I), for example, by the following route: - general formula (IV)
A compound having the herbicidal activity shown in is obtained.
（ｒＶ）
（Ｒ１，Ｒ２，Ｒ３は低級アルキル基を示す）以下に実
施例を挙げて本発明をさらに詳しく説明する。(rV) (R1, R2, R3 represent lower alkyl groups) The present invention will be explained in more detail with reference to Examples below.
（実施例）
２．６−ダニチル−４−フ二ノキシアニリンフェノール
１１．１ｇ、キシレン２００ｍ１及び粉末の水酸化カリ
ウム９．９０ｇの混合物を還流下で４時間加熱した。生
成した水を反応混合物から除去した後、４−ブロモ、２
，６−ジニチルアニリン２２．８ｇ及び塩化第一銅０．
３３ｇを加え、窒素雰囲気下、反応混合物の温度を１６
０〜１７０°Ｃとなるように加熱し、キシレンを留去し
た。反応混合物の温度を１７０°Ｃで４．５時間さらに
２００°Ｃで４．５時間保った。冷却後、反応混合物に
エーテルを加え、ＩＮ ＮａＯＨ次いで飽和食塩水で洗
浄した後、無水硫酸マグネシウムで乾燥し、濃縮した。(Example) A mixture of 11.1 g of 2.6-danityl-4-phynoxyanilinephenol, 200 ml of xylene, and 9.90 g of powdered potassium hydroxide was heated under reflux for 4 hours. After removing the water produced from the reaction mixture, 4-bromo, 2
, 22.8 g of 6-dinitylaniline and 0.5 g of cuprous chloride.
33g was added, and the temperature of the reaction mixture was increased to 16% under nitrogen atmosphere.
The mixture was heated to 0 to 170°C to distill off xylene. The temperature of the reaction mixture was maintained at 170°C for 4.5 hours and then at 200°C for 4.5 hours. After cooling, ether was added to the reaction mixture, which was washed with IN NaOH and then with saturated brine, dried over anhydrous magnesium sulfate, and concentrated.
得られた残さをカラムクロマトグラフィーで精製し、既
記混合物を１５．０ｇ得た。ＩＨＮＭＲ（ＣＤＣ１ａ）
δ１．２１ （６Ｈ、ｔ） 、 ２．５０ （４Ｈ、ｑ
） 、 ３．５７（２Ｈ、ｂｒ） 、 ６．６６ （２
Ｈ、ｓ） 、 ６．４５−７．５０ （５Ｈ、ｍ）。The obtained residue was purified by column chromatography to obtain 15.0 g of the above-mentioned mixture. IHNMR (CDC1a)
δ1.21 (6H, t), 2.50 (4H, q
), 3.57 (2H, br), 6.66 (2
H, s), 6.45-7.50 (5H, m).
Claims (2)
はハロゲン原子を示す。）で表される２，６−ジエチル
−４−フェノキシアニリン誘導体。(1) General formula (I): ▲There are mathematical formulas, chemical formulas, tables, etc.▼(I) 2,6- represented by (R represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, or a halogen atom) Diethyl-4-phenoxyaniline derivative.
式（III） ▲数式、化学式、表等があります▼（III） （Ｍは金属、Ｒは水素原子、低級アルキル基、低級アル
コキシ基又はハロゲン原子を示す。）で表される化合物
とを反応させることを特徴とする一般式（ I ）： ▲数式、化学式、表等があります▼（ I ） （Ｒは前記と同じ意味を示す。）で表される２，６−ジ
エチル−４−フェノキシアニリン誘導体の製造法。(2) General formula (II): ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (II) (X represents a halogen atom) Compound and general formula (III) ▲ Numerical formulas, chemical formulas, tables, etc. General formula (I) characterized by reacting with a compound represented by ▼ (III) (M is a metal, R is a hydrogen atom, a lower alkyl group, a lower alkoxy group, or a halogen atom): ▲ There are mathematical formulas, chemical formulas, tables, etc.▼(I) A method for producing a 2,6-diethyl-4-phenoxyaniline derivative represented by (R has the same meaning as above).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9907088A JPH07107028B2 (en) | 1988-04-21 | 1988-04-21 | 2,6-Diethyl-4-phenoxyalinine derivative and method for producing the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9907088A JPH07107028B2 (en) | 1988-04-21 | 1988-04-21 | 2,6-Diethyl-4-phenoxyalinine derivative and method for producing the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH01272557A true JPH01272557A (en) | 1989-10-31 |
| JPH07107028B2 JPH07107028B2 (en) | 1995-11-15 |
Family
ID=14237596
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP9907088A Expired - Lifetime JPH07107028B2 (en) | 1988-04-21 | 1988-04-21 | 2,6-Diethyl-4-phenoxyalinine derivative and method for producing the same |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH07107028B2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2009132713A (en) * | 2007-11-30 | 2009-06-18 | Saltigo Gmbh | Improved method for catalytic synthesis of diaryl ether |
-
1988
- 1988-04-21 JP JP9907088A patent/JPH07107028B2/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2009132713A (en) * | 2007-11-30 | 2009-06-18 | Saltigo Gmbh | Improved method for catalytic synthesis of diaryl ether |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH07107028B2 (en) | 1995-11-15 |
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